Synthesis of isotopically modified derivatives of dopamine, serotonin and doxorubicine with Boc-Pro and Boc-[2H]Pro

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Abstract


The synthesis of Boc-Pro-Dox, Boc-Pro-DOPA, Boc-Pro-Srt, Pro-Dox, Pro-DOPA, and Pro-Srt, as well as Boc-[2H]Pro-Dox, Boc-[2H]Pro-DOPA, Boc-[2H]Pro-Srt and [2H]Pro-Dox, [2H]Pro-DOPA, and [2H]Pro-Srt were performed for the first time. It was established that Boc-[2H]Pro is the most promising for obtaining deuterated compounds. It was shown that hydrogenation of Boc-APro in ethyl acetate on a palladium catalyst allows 1.6-1.65 times more deuterium to be introduced than for hydrogenation of an unsaturated proline bound to serotonin and three times more than hydrogenating an unsaturated proline bound to dopamine. Due to the instability of doxorubicin under the conditions of the reduction of unsaturated proline, its condensation with Boc- [2H]Pro is the only possibility for obtaining Boc-[2H]Pro-Dox. Mass spectrometric methods determined the content of isotopomers in deuterated products.


About the authors

V. P. Shevchenko

Institute of Molecular Genetics of the Russian Academy of Sciences

Author for correspondence.
Email: nagaev@img.ras.ru

Russian Federation, Moscow

L. A. Andreeva

Institute of Molecular Genetics of the Russian Academy of Sciences

Email: nagaev@img.ras.ru

Russian Federation, Moscow

I. Yu. Nagaev

Institute of Molecular Genetics of the Russian Academy of Sciences

Email: nagaev@img.ras.ru

Russian Federation, Moscow

N. F. Myasoedov

Institute of Molecular Genetics of the Russian Academy of Sciences

Email: nagaev@img.ras.ru

Russian Federation, Moscow

academician of the RAS

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